Author: Jessica.F

Some common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, molecular formula is C13H18N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C13H18N2O2

To a solution of 2-bromo-3-((4-fluorophenyl)ethynyl)pyridine (intermediate 42, 340 mg, 1.23inmol) in anhydrous toluene (15 rnL) was added Pd2(dba)3 (113 mg, 0.123 mmol), XPhos (117 rng,0.246 mmoi) and potassium tert-butoxide (414 mg, 3.69 mrnol) under N2. After 10 mm, tert-butyl5-aminoindoline- I -carboxylate (Intermediate 12, 519 mg, 1.75 mmol) was added and the mixturewas stirred at 20 C for 10 mm, Then, the mixture was heated at 100 C for 3hr, EtOAc and waterwere added. The organic phase was separated and dried (Mg504), filtered and concentrated.Purification IFCC. Si02 0:100 to 30:70, EtOAc/heptane) afforded the title compound (330 mg,62%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 129487-92-9, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BERRY, Cynthia G.B.; CHEN, Gang; JOURDAN, Fabrice Loic; LEBOLD, Terry Patrick; LIN, David Wei; PENA PINON, Miguel Angel; RAVULA, Suchitra; SAVALL, Bradley M.; SWANSON, Devin M.; WU, Dongpei; ZHANG, Wei; AMERIKS, Michael K.; (407 pag.)WO2016/176460; (2016); A1;,
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5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 5332-26-3

A solution of n-butyllithium in THF (1.8 ml, 2.5 M, 4.5mmol) was added in to a cooled mixture of HMDS (608 mg, 4.56 mmol) in THF (20 ml) dropwise over 20 min with stirring. The mixture was stirred for 30 min before benzyl 2-(4- ((cyclopropylmethyl)sulfonyl)phenyl)acetate (1.3 g, 3.8 mmol) in THF (5 ml) was added through a syringe dropwise over 10 min. Stirred for another 30 min at -78 followed by the addition of 2-(bromomethyl)isoindoline-1,3-dione (912 mg, 3.8 mmol) in THF (5 ml) was added through a syringe over 10 min. The mixture was stirred at -78 and allowed to reach to room temperature overnight. The mixture was treated with methanol carefully and the solvents were evaporated. The product was purified by flash chromatography to affod the product as a White solid 1.4 g (74% yield). MS (+) ES: 504 (M+H)+.

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ETERNITY BIOSCIENCE INC.; YAN, Yinfa; ZHANG, Minsheng; LIU, Dong; ZHANG, Fengqi; LIU, Suxing; ZHANG, Rumin; HE, Feng; TAO, Weikang; (211 pag.)WO2019/213470; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 611-09-6, name is 5-Nitroindoline-2,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 611-09-6, Recommanded Product: 611-09-6

General procedure: The preparation was divided into two steps. Firstly, substituent indoline-2,3-dione (1 equiv) was dissolved in ethanol (10 mL), hydrazine hydrate (2 mL) was added. The reaction mixture was refluxed with magnetic stirring for 3 h and cooled to 0 C, then sodium hydroxide (3 equiv) was added, refluxed for 0.5 h and cooled to room temperature, then 150 mL water was added. The mixture was acidified by adding 2 N hydrochloric acid to pH 2, and extracted twice with dichloromethane. The organic filtrate was washed twice with brine, dried (Na2SO4), and then concentrated to give corresponding indolin-2-one by high-vacuum drying. Secondly, a mixture of the corresponding indolin-2-one (1 equiv) and furan-2-carbaldehyde (1 equiv) in ethanol was added two drops of piperidine and refluxed with magnetic stirring for 5 h. After the mixture cooled, the precipitate was filtered, washed with cold ethanol, dried, and recrystallized from methanol to afford the terminal product.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Nitroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhong, Ye; Xue, Mengzhu; Zhao, Xue; Yuan, Jun; Liu, Xiaofeng; Huang, Jin; Zhao, Zhenjiang; Li, Honglin; Xu, Yufang; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1724 – 1734;,
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Some common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, molecular formula is C10H11NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of 3,3-Dimethylindolin-2-one

To a solution of 3,3-dimethylindolin-2-one (1.5 g, 9.31 mmol) in THF (90 mL) was added borane-THF complex (37.3 mL, 37.22 mmol) at 0 C. The reaction was refluxed at 87 C overnight, then cooled to rt, and quenched with MeOH (10 mL). The mixture was reflux at 85 C for 2 h, and then concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as yellow oil (0.87 g, 63.5%). MS (ESI, pos. ion) m/z: 148 [M + H]+; NMR (CDCI3) delta (ppm): 7.11-7.07 (m, 2H), 6.80 (t, 1H), 6.69 (d, 1H), 3.57 (s, 1H), 3.35 (s, 2H), 1.37 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19155-24-9, its application will become more common.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 7699-18-5, name is 5-Methoxyindolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H9NO2

General procedure: To the 3-subtitutedphenyl-1H-pyrazole-5-carbaldehydes 11(a-d) prepared in the above step was added corresponding substituted oxindoles and catalytic amount of piperdine (1.0ml) in ethanol. Heated the reaction mixture to reflux for 4h at 85C. The solid compounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying the final compounds (Z)-3-((3-phenyl-1H-pyrazol-5-yl)methylene)indolin-2-one analogs 12(a-u) were obtained as pure solids (yield 75-80%).

The synthetic route of 7699-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Shaik, Anver Basha; Jain, Nishant; Kishor, Chandan; Nagabhushana, Ananthamurthy; Supriya, Bhukya; Bharath Kumar; Chourasiya, Sumit S.; Suresh, Yerramsetty; Mishra, Rakesh K.; Addlagatta, Anthony; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 501 – 513;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 19155-24-9, name is 3,3-Dimethylindolin-2-one, A new synthetic method of this compound is introduced below., Quality Control of 3,3-Dimethylindolin-2-one

To a mixture of 3,3-dimethyloxindole (409 mg, 2.53 mmol), (S)-3-chloro-1-phenyl-1-propanol (376 mg, 2.20 mmol) and triphenylphosphine (664 mg, 2.53 mmol) in tetrahydrofuran (5 mL) under nitrogen was added slowly diisopropyl azodicarboxylate (490 muL, 2.53 mmol) via a syringe. The resulting solution was stirred at room temperature overnight. Solvent was removed under reduced pressure and the viscous brown liquid residue was purified using Isco CombiFlash Companion chromatography (RediSep 12-g silica column, 0-12percent ethyl acetate/hexane) to give 236 mg (34percent) of 1-[(1R)-3-chloro-1-phenylpropyl]-3,3-dimethyl-1,3-dihydro-2H-indol-2-one as a viscous colorless liquid. MS (ES) m/z 314.1 ([M+H]+); HRMS: calculated for C19H20ClNO+H+, 314.1306; found (ESI, [M+H]+), 314.1299.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Wyeth; US2007/72928; (2007); A1;,
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Reference of 667463-64-1, A common heterocyclic compound, 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

I-5.1 (15.0 g, 63 mmol) and hydrazine hydrate (30 mL, 618 mmol) are heated to 125 C. for 72 h. To the cool reaction mixture DCM is added and extracted with water and 1 M HCl. The organic layer is dried over MgSO4 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed under vacuum. The crystallized product is filtered with sunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 min, LC-MS Method V001-003

The synthetic route of 667463-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275159; (2014); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 65826-95-1, name is 5-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

(1) 1.33 g of 5-methylindoline and 2-chloropyridine were added to a 50 mL round bottom flask, the ratio of the amount of the substance was 1: 1.5; (2) Stir directly in the air and mix evenly at room temperature.Then heated at 80 C, after 45 min, the system solidified, stopped the reaction, and cooled to room temperature; (3) Add 50 mL of saturated NaHCO3 solution to the system to dissolve the solid.Further, 50 mL of ethyl acetate solution was added, shaken, and liquid-separated, and the aqueous phase was extracted three times with ethyl acetate, 30 mL each time, and the organic phase was combined and concentrated by a rotary evaporator; (4) The concentrate was dissolved in 20 mL of ethanol, refluxed at 80 C for 15 min, cooled, and a pale yellow solid was separated, filtered, rinsed with water and dried in vacuo to give the desired product.

The synthetic route of 65826-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Northwest University; Jiao Linyu; Zhang Ze; Yin Xiaomei; Hong Qian; Ning Zihui; Ma Xiaoxun; Li Zhuo; Sun Ming; (11 pag.)CN109265439; (2019); A;,
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Synthetic Route of 3484-35-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3484-35-3, name is 5-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 22 3- [2,4-Dimethyl-5-(5-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrol-3-yl]-propionic acid 3-(2-Carboxyethyl)-2,4-dimethyl-5-formylpyrrole (97.5 mg), 74 mg 5-methyl-2-oxindole, and 75 muL piperidine in 3 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight to give 104 mg (64%) of the title compound as a yellow solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.38 (s, br, 1H, NH-1′), 12.02 (s, br, 1H, COOH), 10.57 (s, br, 1H, NH-1), 7.52 (s, br, 1H, H-4), 7.50 (s, 1H, H-vinyl), 6.87 (d, J=7.86 Hz, 1H, H-6), 6.73 (d, J=7.86 Hz, 1H, H-7), 2.63 (t, J=7.49 Hz, 2H, CH2CH2COOH), 2.34 (t, J=7.49 Hz, 2H, CH2CH2COOH), 2.29 (s, 3H, CH3), 2.28 (s, 3H, CH3), and 2.24 (s, 3H, CH3); MS m/z (relative intensity, %) 325 ([M+1]+, 66).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Methylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
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Electric Literature of 825-70-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 825-70-7 as follows.

General procedure: to a suspension of iv (1mmol) in acetonitrile (10ml) was added 5-fluoroindoline (1.2mmol). The reaction mixture was stirred at 40C for 16h and then evaporated to dryness under reduced pressure. Water (10mL) and diethylether (15mL) were added and the resulting mixture was stirred for 5min. The precipitate formed was filtered off and dried to give 7 (86%) as a white solid.

According to the analysis of related databases, 825-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Certal, Victor; Halley, Frank; Virone-Oddos, Angela; Filoche-Romme, Bruno; Carry, Jean-Christophe; Gruss-Leleu, Florence; Bertin, Luc; Guizani, Houlfa; Pilorge, Fabienne; Richepin, Patrick; Karlsson, Andreas; Charrier, Veronique; Abecassis, Pierre-Yves; Vincent, Loic; Nicolas, Jean-Paul; Lengauer, Christoph; Garcia-Echeverria, Carlos; Schio, Laurent; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1506 – 1510;,
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